Five of Chicago's best rooftop bars

Local award-winning sommelier Regine Rousseau loves rooftop bars almost as much as she loves wine. Here are her top spots in the Windy City, from low-key hangs to ultra luxe champagne lists.

Known as the "Windy City" and notorious for its frigid winters, Chicago might not seem like a natural location for open-air bars. But for sommelier, media personality and events planner Regine Rousseau, it's a perfect pairing.

The SpeciaList

An award-winning writer, speaker and entrepreneur, Regine Rousseau is the founder and CEO of Shall We Wine. She is frequently featured as a wine expert on WGN Chicago and other local television broadcasts, and was named one of the top "40 African-American Tastemakers". She holds a Level II certification from the International Sommelier Guild.

(Credit: Nora Canfield)

"We Chicagoans appreciate a rooftop because we have to deal with the winter," she told BBC. "As soon as it's nice outside, even if you have a winter day where it's sunny… we put our shorts on, we're going outside. And if a restaurant happens to have a patio or rooftop that can be open during the winter, we go in."

The city's rooftop culture is pervasive and enthusiastic: "I don't know if I've ever been to any other city where people talk about 'let's go to a rooftop' like they're talking about a sporting event. It's serious here." A self-proclaimed "sky-hopper", Rousseau frequently scouts the city's rooftops – and their wine lists – to find the perfect backdrop for her clients' mile-high luxury events. "We have such a gorgeous view [in Chicago], so if you can be on the rooftop [where] you can see the view of downtown, that's something that even we natives [appreciate]."

When she's not planning sky scraping soirees or sharing her wine expertise on local media, the Chicago-born Rousseau is a tireless champion for her hometown beyond its nightlife.

"Chicago is the greatest city in the world," she said. "It's a friendly city. You can stop and ask people questions. You can ask someone for recommendations, like, 'Oh, I'm walking down the street; any place good to eat?' We're still that kind of town where people talk to you and people are excited to have you as a tourist."

Here are Rousseau's top five rooftop recommendations in the Windy City.

NoMI Garden

1. Best overall: NoMI at the Park Hyatt

Chicago is full of posh rooftops, but there's one Rousseau can't get enough of: NoMi, found on the seventh floor of the Park Hyatt Chicago on the Magnificent Mile. "That's my favourite," she said of the chic bar and restaurant.

"If you walk past the [hotel's] reception area to go to the rooftop, [it's] like, peace… There's something very minimalist about the décor. It's clean, it's spacious, [there's a lot of] dark wood, but it's still beautifully lit and it's got this really gorgeous, calming scent." NoMi is completely enclosed in glass and offers stunning views of Lake Michigan and Chicago's Water Tower: "There's all the brightness coming in from the city."

The sommelier approves of NoMi's highly curated list of international wines – particularly their sparkling options, which include Laurent Perrier and Lyre's Classico. "It's really my Champagne spot," she said. "It is the place that I go to really explore their wine list."

"It's a beautiful space to have Champagne conversation and just feel calm," she added. "You get to experience Chicago up high, but it's a very quiet side of Chicago."

Website: nomichicago.com

Address: 800 Michigan Ave 7th Floor, Chicago, IL 60611

Phone: (312) 239-4030

Instagram: @nomichicago

Amy Ulivieri

2. Best for Chicago vibes: IO Godfrey Roofscape Bar and Lounge

America's "Second City" has a personality all its own, famously combining Midwest charm with big-city class. Rousseau believes this vibe is embodied by its bars: "[It's] Midwestern with an East Coast influence. What I mean by that is the vibe is: Come as you are, but please come correct."

For Rousseau, the best sky-high "Chicago vibes" are found at the IO Godfrey Roofscape Bar and Lounge. "There's always something going on [there.] The people look good – you can't just show up. You're gonna [have to] dress up a little bit."

The glamorous high-tech space, outfitted with sleek white couches, a retractable roof and a video wall, overlooks the River North and the southern Chicago skyline; its outdoor lounge features igloo reservations and firepits in the winter months, so guests can enjoy the bar's signature cocktail flights and happy hours even in wintertime.

Website: godfreyhotelchicago.com/i-o-rooftop-lounge

Address: 127 West Huron at Lasalle, Chicago, IL 60654

Phone: (312) 374-1830

Instagram: @iogodfrey

Alamy

3. Best for impressing out-of-town visitors: VU

Rather than take visitors to the heavily touristed Loop, Rousseau brings them to Chicago's vibrant South Side; a culturally diverse section of the city brimming with avant garde art galleries, colourful murals and excellent restaurants. "I'm a South Sider, through and through," said Rousseau, who lives in Bronzeville, a neighbourhood historically known as Chicago's "Black metropolis".

Rousseau's favourite neighbourhood rooftop is the elegant, glass-walled VU. Located on the 22nd floor of the Hampton Inn at McCormick Place, the 13,000-sq-ft bar and restaurant serves craft cocktails and brunch dishes like Chicago hot chicken and waffles. The space offers panoramic views of the South Side and the city beyond. "It's very accessible to downtown," she said. "You'll get tourists there because the McCormick Centre is right down the street, and then a lot of local South Siders. I think it's a really gorgeous room [and] the bar is incredibly huge. It's comfortable [with] good music."

Website: vurooftop.com

Address: 133 E Cermak, Chicago, IL 60616

Phone: (312) 256-2990

Instagram: @vurooftop

Daniel Kelleghan Photography

4. Best for a post-shopping lunch: Cindy's

Overlooking Millenium Park with its famous "Bean" sculpture, and surrounded by downtown shopping opportunities, Cindy's is Rousseau's top pick for a delicious post-shopping lunch.

"[It's] super cool because there's a specific [lift] that goes there," she said. "It's in a historic building, the Chicago Athletic Association, so right when you walk in, it's all about Chicago history." The structure, built in 1890, was once home to one of the city's most exclusive members clubs. "They preserved the wood and all the details. You're automatically walking into a space that you feel like something special is about to go down."

High up on the 13th storey of the historic site, Cindy's serves elegant New American cuisine featuring locally-sourced dishes like Pink Moon Oysters, truffle fries and rainbow trout with braised cannellini beans, arugula pistou and chevril. "They have great salads. I know that it sounds boring… but it's hard to find a really good salad to me. They [also] have a grilled cheese and tomato that is delicious."

Rousseau offered an insider tip: "If you can, get a seat on the balcony that overlooks Michigan Avenue and Lake Michigan… You know how you walk into a space and all of a sudden your attitude changes? If you were kind of slumped over, you're like, 'Wait, I'm at Cindy's.'"

Website: https://www.cindysrooftop.com/

Address: 12 S Michigan Ave, Chicago, IL 60603

Phone: (312) 792-3502

Instagram: @cindysrooftop

Bryan at Alebrijes Agency

5. Best for a younger crowd: Panchos Rooftop Cantina

Rooftop culture in Chicago is largely dominated by classy, upscale establishments. But Rousseau has an option that's low-key and sky-high.

"[Panchos Rooftop Cantina!]" she said. "It's super casual … [if] you want to just be easy, you can go there."

The colourful Mexican bar and restaurant takes up two floors, the second of which includes an open rooftop space with a muralled bar area, an extensive margarita list and views of the surrounding South Loop skyline. Happy hours and Mexican street food favourites like elote bites and tacos just add to the festive feel. "It's a younger crowd. If memory serves me right, I think they serve in plastic cups. [There's] loud music. [It's] super different."

Website: panchoschicago.com

Address: 327 S Plymouth Ct, Chicago, IL 60604

Phone: (312) 362-1212

Instagram: @panchos.rooftop

BBC Travel's The SpeciaList is a series of guides to popular and emerging destinations around the world, as seen through the eyes of local experts and tastemakers.

--

If you liked this story, sign up for The Essential List newsletter – a handpicked selection of features, videos and can't-miss news, delivered to your inbox twice a week.

For more Travel stories from the BBC, follow us on Facebook and Instagram.